Glycerol is an extremely useful synthon for the synthesis of many important biochemicals and pharmaceuticals. It can be used as a labeling synthon but has limitations. Glycerol has previously been labeled in a variety of ways with 13C, 14C and 2H. For example, Siskos et al., Tetrahedron Letters, vol. 44, pp. 789-792 (2003) describe the synthesis of [1-13C, 18O] and [1-13C, 2H2]-glycerol; Barber describes the synthesis of [1-13C]-glycerol; and Pitlik et al., J. Labelled Cpd. and Radiopharm., vol. XXXIX, No. 12, pp. 999-1009 (1997) describe the synthesis of 2H- and 13C-labeled glycerols such as [1,1-2H2, 1,2-13C]glycerol. Labeled glycerols can be used in the elucidation of biochemical pathways, e.g., Cho et al., J. Org. Chem., vol. 58, pp. 7925-7928 (1993) describe the incorporation of labeled glycerol samples into the mC7N unit of asukamycin. Some labeled glycerols have also been prepared with chirality, e.g., Nieschalk et al., Tetrahedron: Asymmetry, vol. 8, No. 14, pp. 2325-2330 (1997) describe four stereoisomers of [2H]-glycerol; Matteson et al., J. Am. Chem. Soc., vol. 112, 3964-3969 (1990) describe stereoisomers of deuterated glycerol; and Blackmore et al., Journal of Labelled Compounds, vol. 8, no. 1, pp. 71-76 (1972) describe the preparation of L-[1-14C]-glycerol.
A new synthon, i.e., labeled glycerol, has now been developed that has the synthetic utility of chirality and allows the differentiation of each of the carbons.
It is an object of the present invention to provide chiral labeled compounds useful for synthetic chemistry development.